Tetrahydrocurcumin | Apoptosis Inducer

CAS No. :	36062-04-1
Formula :	C₂₁H₂₄O₆
M.W :	372.41
SMILES Code :	O=C(CC(CCC1=CC=C(O)C(OC)=C1)=O)CCC2=CC=C(O)C(OC)=C2
Synonyms :	HZIV 81-2; NSC 687845; Tetrahydrodiferuloylmethane
MDL No. :	MFCD04152347
InChI Key :	LBTVHXHERHESKG-UHFFFAOYSA-N
Pubchem ID :	124072

Safety of Tetrahydrocurcumin

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of Tetrahydrocurcumin

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 36062-04-1 ]

[ 36062-04-1 ] Synthesis Path-Downstream 1~28

1
[ 458-37-7 ]
[ 36062-04-1 ]

Yield	Reaction Conditions	Operation in experiment
92.9%	With platinum-iron-nickel hydroxide composite nanoparticle catalyst; In ethanol; at 24℃; for 1h;	The platinum - iron-nickel hydroxide composite nano-particle catalyst 1g added curcumin 100 grams,Ethanol 300ml reaction flask, the reaction was stirred at room temperature at 24 ° C for 1 hour, the solvent was evaporated under reduced pressure,98 g pale yellow viscous material was obtained, dissolved in 400 ml ethanol and concentrated to 150 ml,Crystallization was allowed to stand in a freezer to give 92.9 g of a light yellow solid in a yield of 92.9percent.
	With hydrogen;palladium; In ethyl acetate;	The first series of compounds contained two aryl rings separated by an unsaturated seven carbon spacer having two carbonyls. The aryl rings contained different substituents in various positions on the ring, wherein the structure of the substituents was designed to test the importance of the type of functional group and location on the aryl ring necessary for inhibition. The synthesis of compounds 2a-2i was performed using an aldol type reaction as first described by Pabon (Pabon, H. J. J. 1964. A Synthesis of Curcumin and Related Compounds. Recueil 379-386). 2,4-Pentanedione was reacted with a substituted benzaldehyde (FIG. 2) to give curcumin (2a) or one of its analogs (2b-2i). Two curcumin analogs, 3a and 3b were synthesized from analogs 2a and 2b according to the scheme found in FIG. 2, using palladium on activated charcoal under a hydrogen atmosphere. These compounds contain two aryl rings separated by a saturated seven carbon spacer having two carbonyls and were designed to test the importance of having saturation in the seven carbon spacer. Four additional curcumin analogs, 4b, 5b, 6b, and 7b were synthesized from analog 2b according to the scheme found in FIG. 2. These contain two aryl rings separated by an unsaturated seven carbon spacer having at least one substituent between the carbonyls. These two curcumin analogs were designed to test the importance of substituents on the spacer and on the central methylene carbon. The synthesis of compounds 4b and 5b was performed by addition of a base and an alkyl halide in an SN2 type reaction. The disubstituted compound 5b was formed rather than the monosubstituted compound 7b. Compounds 6b and 7b were prepared, respectively, by reacting 3-methyl-2,4-pentanedione and 3-benzyl-2,4-pentanedione with benzaldehydes in an aldol type reaction.
	With palladium 10% on activated carbon; hydrogen; In ethyl acetate;	Gingerenone A utilized in the present invention was synthesized by hydrogenating and dehydrating curcumin, which is a natural material extracted from turmeric root according to the process shown in FIG. 1. A constitutional formula of the synthesized compound is identical to the above Formula 1.

References: [1]Patent: CN104496779,2017,B .Location in patent: Paragraph 0014; 0015; 0016; 0017; 0018-0023.
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2001,vol. 40,p. 495 - 497.
[3]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 6175 - 6181.
[4]Bioscience, Biotechnology and Biochemistry,1995,vol. 59,p. 1609 - 1612.
[5]Biochemical Pharmacology,1996,vol. 52,p. 519 - 525.
[6]American Chemical Journal,1882,vol. 4,p. 360.
[7]Chemische Berichte,1914,vol. 47,p. 2999.
[8]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3811 - 3820.
[9]Patent: US2006/258752,2006,A1 .Location in patent: Page/Page column 4; sheet 1.
[10]Food Chemistry,2013,vol. 136,p. 650 - 658.
[11]Patent: US2016/74338,2016,A1 .Location in patent: Sheet 1.

2
[ 98885-93-9 ]
[ 36062-05-2 ]
[ 36062-04-1 ]
[ 36062-07-4 ]

References: [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 3481 - 3487.
[2]Phytochemistry,1990,vol. 29,p. 797 - 799.
[3]Journal of Medicinal Chemistry,2002,vol. 45,p. 5037 - 5042.

3
[ 36062-04-1 ]
[ 113464-93-0 ]

References: [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 518 - 525.

5
[ 36062-04-1 ]
[ 36062-05-2 ]

Yield	Reaction Conditions	Operation in experiment
40 g	With methanol; sodium tetrahydroborate; at 0 - 25℃;	Gingerenone A utilized in the present invention was synthesized by hydrogenating and dehydrating curcumin, which is a natural material extracted from turmeric root according to the process shown in FIG. 1. A constitutional formula of the synthesized compound is identical to the above Formula 1.

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2001,vol. 40,p. 495 - 497.
[2]Patent: US2016/74338,2016,A1 .Location in patent: Sheet 1.

6
[ 98885-93-9 ]
[ 36062-04-1 ]

References: [1]Arzneimittel-Forschung/Drug Research,2002,vol. 52,p. 120 - 124.

7
[ 36062-04-1 ]
[ 36062-07-4 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium tetrahydroborate; In tetrahydrofuran; at 20℃; for 5h;	Sodium borohydride (230 mg, 6.0 mmol) was added to a solution of tetrahydrocurcumin(1.12 g, 3.0 mmol) in anhydrous tetrahydrofuran (THF) (15 mL) and the solution stirredat room temperature for 5 hours. At this time, TLC [(30 pL aliquot into saturatedNH4CI:EA (400 pL:400 pL); eluting with EA:hexane (75:25)], showed the formation of amajor product. The reaction mixture was diluted with 0.3 N HCI (150 ml) and extractedwith EA (3 X 50 mL). The organic layer was dried with Na2504, filtered and the solvents removed under reduced pressure to give a colorless oil (1 .2 g). The crude product waspurified by FC on silica gel eluting with EA:hexane (80:20) to give pure product formula4 as a colorless gel (1 .Og, 89percent). HPLC-UV showed >99percent purity; LC-MS (ESI+)showed expected mass [M+H] 341.1 (-2H20); 1H NMR (400 MHz, ODd3) D 6.67-6.81(6H, m), 3.99 (1H, m), 3.90 (1H, m), 3.87 (6H, s), 2.61-2.69 (4H, m), 1.61-1.78 (6H, m).

References: [1]Patent: WO2018/149578,2018,A1 .Location in patent: Page/Page column 17; 18.
[2]Arzneimittel-Forschung/Drug Research,2002,vol. 52,p. 120 - 124.

8
[ 121-33-5 ]
5-fluoro-2-trifluoromethylbenzyl halide [ No CAS ]
[ 36062-04-1 ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3811 - 3820.

9
[ 123-54-6 ]
[ 36062-04-1 ]

References: [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 3811 - 3820.

10
[ 36062-04-1 ]
1,7-bis-(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-acetonide [ No CAS ]

References: [1]Arzneimittel-Forschung/Drug Research,2002,vol. 52,p. 120 - 124.

11
[ 36062-04-1 ]
[ 79067-88-2 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2001,vol. 40,p. 495 - 497.

12
[ 36062-04-1 ]
[ 41137-87-5 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2001,vol. 40,p. 495 - 497.

Yield	Reaction Conditions	Operation in experiment
		Tetrahydrocurcumin (11). White powder, mp 92-93° C. (Roughley et al., J. Chem. Soc. Perkin I, 2379-2388 (1973), 95-96° C.), 1H NMR (300 MHz, CDCl3): delta 2.53-2.58 (3H, m), 2.78-2.88 (5H, m), 3.87 (6H, s, OCH3*2), 5.43 (1H, s, 1-H), 5.50 (2H, s, ArOH), 6.65 (2H, d, J=8 Hz), 6.69 (2H, s), 6.83 (2H, d, J=8 Hz); 13C-NMR (300 MHz, CDCl3): delta 31.3, 40.4, 55.8, 99.8, 111.0, 114.3, 120.8, 132.6, 144.0, 146.4 and 193.2.
	With hydrogen; In isopropyl alcohol; at 50 - 55℃; under 3750.38 Torr; for 6h;	General procedure: b) Synthesis of 1,7-Bis-(4-methoxyphenyl)-3,5-heptanedione (formula 3) 270 g of the wet cake obtained in experiment 1.1.a is dissolved in 1600 g isopropanol, 5 g Raney Nickel are added and then this mixture is hydrogenated at 5 bar and 50-55° C. during 6 h. After filtration of the catalyst the product is crystallized from the solution by cooling down to 20° C. The white product is filtered, dried and 175 g product are achieved (purity >95percent, yield 50percent over two steps).

14
[ 36062-04-1 ]
[ 5470-11-1 ]
[ 113465-11-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium acetate; In ethanol; ethyl acetate;	EXAMPLE 12 3,5-Bis[beta-(4'-hydroxy-3'-methoxyphenyl)ethyl]isoxazole 1,7-Bis(4'-hydroxy-3'-methoxyphenyl)-3,5-heptadione (1.00 g, 2.7 mmoles) (Bull. Acad. Polon. Sci. 6, 481-486, 1958), hydroxylaminehydrochloride (0.19 g, 2.7 mmoles), and sodium acetate (0.44 g, 5.4 mmoles) are dissolved in 50 ml of 95percent ethanol. The reaction is stirred at reflux overnight. The solvent is removed, and the residue is taken up in ethyl acetate. The ethyl acetate solution is washed with water and dried over magnesium sulfate. A precipitate forms on standing at room temperature for 2 days, and it is collected by filtration to give a white solid. The solid is taken up in 20 ml of ethanol containing 0.5 ml of 2N hydrochloric acid. The solution is heated to reflux for one hour. After neutralization with sodium bicarbonate, the ethanol is evaporated, and the residue is partitioned between ethyl acetate and water. The organic layer is dried over magnesium sulfate and passed through a silica gel plug which is washed with 1:1 ethyl acetate/hexane. Evaporation of the solvent gives 0.2 g of the product obtained as a hydrate. mp=106°-107° C. Analysis for C21 N25 NO6 *0.4 mole H2 O. Calculated C-66.97, H-6.38, N-3.72. Found C-67.13, H-6.41, N-3.47.

References: [1]Patent: US4877881,1989,A .

15
[ 458-37-7 ]
[ 36062-05-2 ]
[ 36062-04-1 ]
[ 36062-07-4 ]

References: [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 941 - 956.
[2]European Journal of Medicinal Chemistry,2010,vol. 45,p. 4446 - 4457.

16
[ 36062-04-1 ]
C₂₁H₂₅NO₆ [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 4446 - 4457.

17
[ 115945-70-5 ]
[ 458-37-7 ]
4,4'-di-O-(β-D-glucopyranosyl)curcumin [ No CAS ]
[ 387818-26-0 ]
[ 1352455-17-4 ]
[ 1352455-15-2 ]
hexahydrocurcumin-O-glucoside [ No CAS ]
[ 36062-05-2 ]
[ 36062-04-1 ]
[ 36062-07-4 ]
(E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hept-1-ene-3,5-dione [ No CAS ]
(1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-diol [ No CAS ]

References: [1]Biocatalysis and Biotransformation,2010,vol. 28,p. 380 - 386.

18
[ 458-37-7 ]
[ 917909-26-3 ]
[ 36062-04-1 ]

References: [1]Proceedings of the National Academy of Sciences of the United States of America,2011,vol. 108,p. 6615 - 6620.

19
[ 458-37-7 ]
[ 36062-04-1 ]

References: [1]Proceedings of the National Academy of Sciences of the United States of America,2011,vol. 108,p. 6615 - 6620.

20
[ 458-37-7 ]
[ 36062-05-2 ]
[ 36062-04-1 ]

References: [1]Natural Medicines,2012,vol. 66,p. 400 - 405.

21
[ 36062-04-1 ]
[ 551-93-9 ]
[ 1408335-41-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	With trifluoroacetic acid; at 100℃; for 0.666667h;	2-Aminoacetophenone (0.675 g, 5 mmol) was taken in a roundbottomed flask along with THC (2.23 g, 6 mmol). To this was added TFA (2?3 mL) and the mixture stirred at 100 C for 40 min. The progress of the reaction was monitored by TLC. Also, the formation of a solid mass was noticed towards completion of the reaction. It was then neutralised with saturated NaHCO3 solution (100 mL). The solid that separated was filtered, washed with water and dried. The resultant crude material was then triturated using ethyl acetate and petroleum ether. The material at this stage was dried in a desiccator over fused CaCl2 for 12 h. Yield: 1.98 g, 84percent. Light yellow solid; m. p. 112?115 C; 1H NMR: d 8.17 (d, J = 8.3 Hz, 1H, H-8), 7.98 (d, J = 8.3 Hz, 1H, H-5), 7.7 (ddd, J1 = 8.6 Hz, J2 = 6.8 Hz, J3 = 1.2 Hz, 1H, H-7), 7.6 (ddd, J1 = 8.3 Hz, J2 = 6.9 Hz, J3 = 1.1 Hz, 1H, H-6), 6.84 (d, J = 8 Hz, 1H, H-26), 6.81 (d, J = 8 Hz, 1H, H-19), 6.75 (d, J = 1.4 Hz, 1H, H-29), 6.73 (d, J = 1.9 Hz, 1H, H-16), 6.70 (dd,J1 = 7.9 Hz, J2 = 1.9 Hz, 1H, H-25), 6.63 (dd, J1 = 8 Hz, J2 = 1.8 Hz, 1H, H-20), 5.79 (br, 2H, Hydroxyls at C-27 & C-18), 3.82 (s, 3H, H-30), 3.78 (s, 3H, H-21), 3.04?3.08 (m, 4H, H-23 & H-14), 3.0?3.04(m, 4H, H-13 & H-22), 2.48 (s, 3H, H-11); 13C NMR: d 207.27(C-12),155.40 (C-2), 146.29 (C-27), 146.20 (C-18), 146.09 (C-10), 143.92(C-28), 143.69 (C-17), 139.87 (C-4), 135.05 (C-3), 133.02 (C-24),131.89 (C-15), 129.89 (C-7), 128.53 (C-8), 126.45 (C-6), 125.82 (C-9), 123.36 (C-5), 120.68 (C-25), 120.66 (C-20), 114.25 (C-26),114.04 (C-19), 111.06 (C-16 & C-29), 55.56 (C-30), 55.50 (C-21),47.16 (C-13), 38.61 (C-14), 35.10 (C-23), 28.69 (C-22), 15.04 (C-11); mass: calculated 471.2046; found; [M+ + 1] = 472.8925.

References: [1]Food Chemistry,2013,vol. 136,p. 650 - 658.

22
[ 36062-04-1 ]
[ 2835-77-0 ]
[ 1408335-42-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	With trifluoroacetic acid; at 100℃; for 0.5h;	General procedure: In a typical reaction, 2-aminoacetophenone, 2-aminobenzophenone or a substituted 2-aminobenzophenone (5 mmol) was added with THC or zingerone (6 mmol) into a round-bottomed flask. To this mixture, TFA (2?3 mL) was added and stirred at 100 C for the period mentioned in Tables 1 and 2. After completion of the reaction, as indicated by TLC analysis, the reaction mixture was neutralised with 100 mL of saturated sodium bicarbonate solution. The solid that separated was filtered and washed with distilled water and dried. The resultant crude material was further purified by triturating with ethyl acetate and petroleum ether (60?80 C). It was then dried in a desiccator over fused calcium chloride for 12 h. The physical and spectroscopic data of individual pure compounds is presented below.

References: [1]Food Chemistry,2013,vol. 136,p. 650 - 658.

23
[ 36062-04-1 ]
[ 1775-95-7 ]
[ 1408335-43-2 ]

Yield	Reaction Conditions	Operation in experiment
65%	With trifluoroacetic acid; at 100℃; for 2h;	General procedure: In a typical reaction, 2-aminoacetophenone, 2-aminobenzophenone or a substituted 2-aminobenzophenone (5 mmol) was added with THC or zingerone (6 mmol) into a round-bottomed flask. To this mixture, TFA (2?3 mL) was added and stirred at 100 C for the period mentioned in Tables 1 and 2. After completion of the reaction, as indicated by TLC analysis, the reaction mixture was neutralised with 100 mL of saturated sodium bicarbonate solution. The solid that separated was filtered and washed with distilled water and dried. The resultant crude material was further purified by triturating with ethyl acetate and petroleum ether (60?80 C). It was then dried in a desiccator over fused calcium chloride for 12 h. The physical and spectroscopic data of individual pure compounds is presented below.#10;

References: [1]Food Chemistry,2013,vol. 136,p. 650 - 658.

24
[ 36062-04-1 ]
[ 719-59-5 ]
[ 1408335-44-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With trifluoroacetic acid; at 100℃; for 0.666667h;	General procedure: In a typical reaction, 2-aminoacetophenone, 2-aminobenzophenone or a substituted 2-aminobenzophenone (5 mmol) was added with THC or zingerone (6 mmol) into a round-bottomed flask. To this mixture, TFA (2?3 mL) was added and stirred at 100 C for the period mentioned in Tables 1 and 2. After completion of the reaction, as indicated by TLC analysis, the reaction mixture was neutralised with 100 mL of saturated sodium bicarbonate solution. The solid that separated was filtered and washed with distilled water and dried. The resultant crude material was further purified by triturating with ethyl acetate and petroleum ether (60?80 C). It was then dried in a desiccator over fused calcium chloride for 12 h. The physical and spectroscopic data of individual pure compounds is presented below.#10;

References: [1]Food Chemistry,2013,vol. 136,p. 650 - 658.

25
[ 18330-94-4 ]
[ 36062-04-1 ]
[ 1408335-45-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With trifluoroacetic acid; at 100℃; for 1.5h;	General procedure: In a typical reaction, 2-aminoacetophenone, 2-aminobenzophenone or a substituted 2-aminobenzophenone (5 mmol) was added with THC or zingerone (6 mmol) into a round-bottomed flask. To this mixture, TFA (2?3 mL) was added and stirred at 100 C for the period mentioned in Tables 1 and 2. After completion of the reaction, as indicated by TLC analysis, the reaction mixture was neutralised with 100 mL of saturated sodium bicarbonate solution. The solid that separated was filtered and washed with distilled water and dried. The resultant crude material was further purified by triturating with ethyl acetate and petroleum ether (60?80 C). It was then dried in a desiccator over fused calcium chloride for 12 h. The physical and spectroscopic data of individual pure compounds is presented below.#10;

References: [1]Food Chemistry,2013,vol. 136,p. 650 - 658.

26
C₁₉H₁₃Cl₂NO [ No CAS ]
[ 36062-04-1 ]
1-(6-chloro-4-(2-chlorophenyl)-2-(4-hydroxy-3-methoxyphenethyl)quinolin-3-yl)-3-(4-hydroxy-3-methoxyphenyl)propan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With trifluoroacetic acid; at 100℃; for 1h;	General procedure: In a typical reaction, 2-aminoacetophenone, 2-aminobenzophenone or a substituted 2-aminobenzophenone (5 mmol) was added with THC or zingerone (6 mmol) into a round-bottomed flask. To this mixture, TFA (2?3 mL) was added and stirred at 100 C for the period mentioned in Tables 1 and 2. After completion of the reaction, as indicated by TLC analysis, the reaction mixture was neutralised with 100 mL of saturated sodium bicarbonate solution. The solid that separated was filtered and washed with distilled water and dried. The resultant crude material was further purified by triturating with ethyl acetate and petroleum ether (60?80 C). It was then dried in a desiccator over fused calcium chloride for 12 h. The physical and spectroscopic data of individual pure compounds is presented below.#10;

References: [1]Food Chemistry,2013,vol. 136,p. 650 - 658.

27
[ 36062-04-1 ]
[ 100-52-7 ]
[ 57-13-6 ]
[ 1432038-10-2 ]

Yield	Reaction Conditions	Operation in experiment
74%		General procedure: To a solution of the corresponding aromatic aldehyde (0.27 mmol) in EtOH (0.5 mL) was added urea (0.54 mmol) and CuSO4·5H2O (0.054 mmol). The mixture was stirred at 80 °C for 15 minutes before tetrahydrocurcumin or tetrahydrodemethoxycurcumin (0.27 mmol) was added. The reaction mixture was continued stirring for 24 hours and quenched with water (2 mL). The solution was washed with water (10 mL) and extracted with EtOAc (415 mL). The combined organic phases were washed with brine, dried over MgSO4 and concentrated under reduced pressure to afford crude product as a yellow brown oil. Purification was accomplished by column chromatography eluting with 60percent-75percent EtOAc/hexane to furnish compounds 8-17.

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2880 - 2882.

28
[ 36062-04-1 ]
[ 99-61-6 ]
[ 57-13-6 ]
[ 1432038-13-5 ]

Yield	Reaction Conditions	Operation in experiment
59%		General procedure: To a solution of the corresponding aromatic aldehyde (0.27 mmol) in EtOH (0.5 mL) was added urea (0.54 mmol) and CuSO4·5H2O (0.054 mmol). The mixture was stirred at 80 °C for 15 minutes before tetrahydrocurcumin or tetrahydrodemethoxycurcumin (0.27 mmol) was added. The reaction mixture was continued stirring for 24 hours and quenched with water (2 mL). The solution was washed with water (10 mL) and extracted with EtOAc (415 mL). The combined organic phases were washed with brine, dried over MgSO4 and concentrated under reduced pressure to afford crude product as a yellow brown oil. Purification was accomplished by column chromatography eluting with 60percent-75percent EtOAc/hexane to furnish compounds 8-17.

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2880 - 2882.

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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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